


When a Boy Goes Bad

by tylerty97



Category: Supernatural
Genre: Fluff, Gay, Gay Male Character, Gay Sex, M/M, Plot, Smut, Storyline
Language: English
Status: In-Progress
Published: 2016-08-12
Updated: 2017-04-23
Packaged: 2018-08-08 07:15:12
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 3,265
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7748218
Author URL: https://archiveofourown.org/users/tylerty97/pseuds/tylerty97
Summary: <blockquote class="userstuff">
              <p>This story is my first real story that has a plot and progressing story. Enjoy :)</p>
            </blockquote>





	1. The disappearance of Sam

       The night started out quiet for the brothers. They did their usual of sitting in a tiny motel room drinking beers and eating cheap takeout food. Normally they loathed this type of night, but at this moment, nothing sounded nicer. They had followed a trail of demons earlier in the week, tracking 4 disappearances, all 4 having the smell of sulfur in the victims’ homes.  
They tracked the demons to an old abandoned factory where nothing but empty conveyers and lifeless machines stood idle. Sam and Dean thought it would be a quick fix, they thought it was just one lowly crossroads demon. Boy, were they wrong.

  
      “Sammy! Wake up!” Dean half shouted, half whispered, “dammit Sammy! Cas! We need your help”  
Sam shifted slightly and groaned, but still appeared to be unconscious. Both brothers were tied securely to a pole in the middle of a dark, dusty, and old room. Dean struggled against the rough rope, pulling and pushing against the knots. They seemed almost enchanted and impossible to push loose. Footsteps echoed in the hall outside the office room and multiple voices came muffled through the door. Dean pushed harder against his ropes, causing his wrists to scrape and bleed a bit.  
       

        “All these years of hunting, a trip to hell and purgatory, just to be wiped out tied up by some damn crossroad demons,” Dean thought to himself. “CAS, WE NEED YOU!” He shouted once more.  
The door squeaked open and 3 dark figures stepped in, one in a dark over coat, the other two in fresh pressed suits. The smell of rotting eggs suddenly swarmed the room. The light flicked on, causing Dean to squint his eyes.  
 

         “Hello Moose, Squirrel, it’s been a while, hasn’t it?” Crowley’s Scottish accent flowed through the room like a wave in the ocean. “Looks like you two got yourselves into quite the situation. I caught wind that you boys were hunting my personal affiliates in this area and we can have none of that, now.”

          “What did you expect? We hunt you assholes,” Dean spat back. “Why are you wasting your time in this hole?”  
 

          “For simplicity, Squirrel. I won’t be keeping you here long, so why go all out? You can handle this, right?” The condescending tone ripped against Dean’s eardrums like a dull knife through flesh. Crowley snapped his fingers and his affiliates were gone. The King walked over to Sam, roughing up his hair and slicking it out of his face. “Moose is really out, isn’t he?”

           “Don’t you touch him, you son of a bitch!” Dean desperately screamed. He pulled against his bonds, opening his wrists again.

        “Now now, don’t go hurting yourself now,” Crowley calmly said, waving a hand and sealing up the rope wounds. He untied Sam and leaned the massive man against him. “Don’t you worry about me or old Moose here. I won’t be hurting him, I swear on my kingdom.” And with that, Crowley snapped his fingers. Dean’s restraints were gone, but so were Crowley and Sam.  
         

         “Sam no! Cas! I need your help!” Dean shouted, standing up and arming himself with the demonblade. He immediately started heading back to the hotel to start his search for Sam. Where in the world, or other worlds, would Crowley take Sam?

 

         Dean shuffled through everything he had on Crowley, demons, and Hell. Papers were spread everywhere, coffee cups and beer bottles thrown haphazardly on the floor, and the bed thrashed in as if nightmare after nightmare was experienced in it, which it was. It had been a week and there were no signs of Sam or Crowley, and Dean saw nothing but pain, torture, and death of Sam in his dreams. Not even Castiel had shown up to even sooth Dean. He felt so alone and lost. His brother was gone with Crowley and his only angelic friend was MIA. He had tortured 6 demons looking for a way in to Hell with no success. Dean felt defeated. 

 

        "I swear on my grave Crowley, if you hurt one excessively long hair on Sam's head, I will destroy you," he whispered under his breath. 

 

         A familiar voice called out in protest and Dean felt himself stiffen with shock, relief, and anger.


	2. Hot and Heavy

**Summary for the Chapter:**

> Sam learns why Crowley has kidnapped him.

**Notes for the Chapter:**

> This one is almost entirely smut lolol  
> If you want more, leave comments, criticism, and kudos. I'll be happy to write more.

        Crowley lead a dazed and confused Sam through the intricate hallways of the Palace of Hell. Demonic runes as old as time were carved into the smooth, warm stone walls. Sam could read some of them, gathering that they told the story of Lucifer and the prophecy of how he would rise to power and ultimately fall. He shuffled along, trying to keep up with Crowley. 

 

        "Impressive, isn't it," Said Crowley casually. "They were all carved by the very first inhabitants of Hell, the first souls to be tortured." He turned a corner and pressed a raised rune in to the wall, opening a doorway in the seemingly solid stone. It opened to a large bedroom with a king sized bed, a stocked bar counter, a couple chairs, a loveseat, and a dresser. Crowley gestured for Sam to enter first. The room was significantly cooler than the rest of Hell. It felt air conditioned and sat at a comfortable 70 degrees. The smell of sulfur and blood were also absent. Instead, the aroma of fresh laundry, pleasant whiskey, and faint roses filled the air. Sam cautiously moved through the room and sat in one of the suede chairs. 

 

        "Don't be so skittish, Moose, I haven't brought you here to hurt you. Quite the opposite, really," the words rolled off his tongue and through the air. 

 

        "Then why am I here?" Inquired Sam, leaning back and relaxing slightly.

 

        Crowley moved towards Sam, sitting on the arm of the chair he was sitting in. "I have a proposal for you. Ever since you lost your soul, I've had a strange physical attraction to you. Even you gaining your soul again didn't deter me." The words came off more blunt than he intended. He shifted to face Sam better, deciding against adding more to explanation. "So I've brought you here to a bedroom stocked with your favorite alcohols, a roomy bed, and sulfur free air in hopes you'll entertain my fantasies." 

 

        Sam was completely speechless. The King of Hell just admitted to him that he was attracted to him and wished to have sex with him. It was only deciding if he should go for it or not. After all, Sam also had some quite perverse thoughts about dear old Crowley. His rough voice mixed with the British accent made Sam melt into puddles in his dreams. The hunter decided quickly and spoke. "I want to. I never thought this would happen."

 

       "Well then, Sam Winchester, let me fetch us some drinks while you get comfortable," Crowley said, motioning to the bed as he moved to the bar counter. For Sam, Crowley pours a large glass of stout whiskey over some chilled stones, swirling the strong liquid around before putting it down. For himself, he mixes a fruity cocktail with rum and strawberries. Sam had already moved to the bed and unbuckled his belt and pants and removed his shoes. Crowley brought the two drinks over to the oversized hunter, handing him the whiskey and downing half of his own drink. Sam swallowed the whole glass of whiskey in one go, feeling it go straight to his head, since he had an empty stomach. 

 

        Sam wrapped an arm around Crowley's waist, pushing the overcoat off with his other hand. He felt bold doing this, as Sam felt like he would be possibly a bottom but had no plans to give in to such. He stood up, letting his jeans fall to the floor, kicking them off as well. Crowley let his coat fall to the floor and join Sam's jeans, removing his shirt, belt, and shoes as well. He felt his humanity start to return, his desire to be loved and held and caressed flooded him, causing him to melt into Sam. He unbuttoned the hunter's flannel shirt, removing it swiftly and pulled off the undershirt underneath, leaving the toned and attractive body of Sam Winchester. He ran his hand over Sam's chest and abdomen, feeling his penis start to stir in his pants. He stood back and admired the hunter, standing there in his tight boxer briefs, showing off a large  bulge. Crowley unbuttoned his own pants, kicking them off and to the side, then dropping his boxers, exposing his impressive 11 inch cock. 

 

       Sam's jaw dropped in awe. He had never seen a dick that big. He felt his own 8 incher start to stir, causing a wet spot to form in his boxer briefs. "Holy shit, Crowley. I'm not sure I can take all of that in me," Sam stated bluntly.

 

      "Don't worry, Moose. You can fuck me first and we'll see how it goes," Crowley reassured, stepping towards Sam and dropping to his knees in front of him. He tugged at the waistband of Sam's underwear, pulling down and releasing his semi erection. He took the hunter's dick in his mouth, taking as much as he could in one quick motion, causing Sam to buck his hips and push deeper. Crowley suckled on his member until it was throbbing and hard as marble. He stood and moved to the bed, grabbing a bottle of lube on his way over and laid down on his side, Sam followed close behind. 

 

      "You don't have to work me too much, Moose, I'm the King of Hell, I can loosen myself on command," Crowley stated, lifting his leg and squirting lube on his hand and in Sam's hand. He slicked the lube over his anus and moaned slightly, pleased at his own touch. Sam scooted up behind him, his hard cock pressing in to Crowley's asscheek. He went straight for gold and pushed 3 fingers in to Crowley's anus, spreading them inside. Crowley flinched and gasped at the sudden and large intrusion, but pushed back on his fingers and moaned. Sam continued to stretch Crowley's ass and teased is prostate, causing his 11 incher to twitch and stand at full attention. He withdrew his fingers and spread the remaining lube over his hard cock, pressing it against Crowley's stretched anus. He pushed until he felt himself pop inside and pushed himself in one quick stroke balls deep. 

 

         Crowley felt the wind knocked out of him, granted he wasn't used to taking cock, but he was sure Sam had to be more than the 8 inches he thought he was to do that to him. He groaned as Sam pumped in and out of him, feeling the hunter's balls slap against his own balls. Sam reached around and stroked his cock, paying extra attention to the head. He grabbed the King's leg and pushed it up higher to allow deeper fucking. Crowley started moaning in quick and loud bursts and Sam pummeled into his prostate, causing his own cock to leak. He felt himself suddenly empty as the hunter withdrew his cock. "Roll on your back," Sam said as he threw a pillow over Crowley's head to cover his eyes. Sam squirted some lube on his hand and rubbed up over his own asshole, massaging it and walking to the dresser. He opened the dresser and found the most diverse assortment of sex toys he had ever seen. He grabbed a peculiar looking buttplug that was textured like dragon skin.

 

        Sam walked back over to the bed, lubing the buttplug, which also turned out to vibrate, and crawled back to Crowley. He inserted the buttplug in to Crowley slowly, earning a grunt from the King of Hell. He switched it to pulsing vibrations and let it go. Sam pulled the pillow off of Crowley's face and straddled him, rubbing his own cock against the impressive 11 incher. He took a breath and lubed up Crowley's cock and aimed it towards his anus, pushing against his hardness. "Sam, are you sure about this? We haven't even worked you open," Crowley protested. But it was too late. Sam had already pushed himself balls deep on to Crowley's massive member. He sat still, waiting for himself to adjust to the intrusion. Surprisingly, it didn't hurt, he just felt very very full and he felt like his lungs were being poked. 

 

      The King started moving slowly, in and out of Sam's tight ass, groaning at the heat surrounding his cock. He felt himself involuntarily buck harder every time Sam squeezed around him. He picked up his pace and soon they were moving in unison, pumping, humping, grunting, and sighing as each took their pleasure. Sam reached behind him, between Crowley's legs and gripped the outside of the buttplug. He switched the vibrations to high and pushed it hard at an angle that assaulted Crowley's prostate. Crowley, in response, bucked hard into Sam's ass, moaning his name and smashing in to his prostate as well. "Sam I'm gonna cum. I'm so close," Crowley grunted, sweat beading on his forehead. He pumped faster and faster until he felt Sam tense up and half moan half scream in pleasure. Sam spewed his cum all over Crowley's chest, as Crowley himself emptied the contents of his testicles in to his ass. The vibrations from the buttplug caused a second round of ejaculate and orgasmic bliss to shoot through Crowley's body and in to Sam. 

 

      "Well, I'll be damned, Moose," panted Crowley as he pulled his softening cock out of Sam and shut off the buttplug. "That's the most intense orgasm I've had in 100 years."

 

      "I've never cum from someone fucking my ass," Sam responded, catching his breath, still half moaning. He felt Crowley's cum leaking out of his ass and on to the bed. "Why didn't we do this sooner?"

 

     "Simple. Hunters don't screw demons, much less the King of demons," Crowley responded, his dick swaying as he went to grab them both a whiskey. "We will be doing this more often, and I have a whole arsenal of toys to use on that tight ass of yours." 


	3. A Familiar Face

**Summary for the Chapter:**

> Dean sees a face he thought was gone for good

**Notes for the Chapter:**

> It's been a while since I updated. I got busy with work and such. But I'm back with i dont even know how to describe this.

 "Bobby?! What the hell are you doing here? Aren't you supposed to be in heaven drinking beer and being happy?" Dean asked.

 

      Bobby took his hat off and brushed his balding hair back and replaced it back on his head. "I don't even get a hug?" He shot back. Dean hugged him like there had been 20 years since they last saw each other. "Before you ask, I have no idea why I'm here, either," stated Bobby. 

 

       "I've been praying and calling for Cas for help. Crowley took Sam, I was sloppy," Dean said. "Is it possible he sent you?"

 

        "It's possible, but what could I do to help with that? I'm just a ghost," Bobby replied in a gruff tone. "There's literally nothing I could do."

 

        Dean sighed and collapsed into a chair, opening a beer and offering one to Bobby. The two men shared a moment of silence, both deep in thought on how to rescue Sam from Crowley. Dean still didn't know what to do. He was relieved to see Bobby again, but angry that it wasn't Cas who answered his prayers.  _Cas is the one with the powers and angel mojo,_ he thought to himself.  _I need power to get Sam out of there._  Bobby piped up. 

 

        "Doesn't look like reading the lore or torturing demons will do much more. Seems you've already done plenty of that. Have you tried reaching out to other angels?" He said, knowing Dean despises all angels except Cas. The younger man furrowed his brow, putting his hand to his head.

 

            “You know I hate other angels. They’re just as evil as demons.”

 

            “I know, son. But what are we supposed to do? We don’t have angel OR demon mojo for ourselves.” Bobby pointed out. “I hate the idea too but it seems like it’s our only choice.”

            Dean sat in thought for a moment, taking another long swig of beer. He pondered his choices. He could call other angels, potentially making him a God Squad target, or he and Bobby could try and do this on their own, which for all they know could be impossible. He sighed deeply, stood up, and turned to Bobby.

            “No angels. The God Squad is out of this one except for Cas.” He said in a commanding tone. He prayed as hard as he could to Castiel, begging him to come to his side and help them. _Cas, I need you. I need you so bad right now._

            “Alright I suppose we should gear up then and prepare?” Bobby said, moving towards the door. Dean followed with the keys to the Impala in his hand.

            The wind blew hard, not even his heavy leather jacket and the layers of flannel underneath were breaking the cold. Dean shivered, wishing his warm, protective angel was here. He tucked his arms in tight and walked through the woods with Bobby at his side, searching for the Impala. Castiel appears behind Dean, the soft glow around his wings fading as they fold into his back.

            “Dean.” His gruff voice calls out, his trench coat blowing in the wind.

            “Cas?” Dean swings around, nearly dropping the keys to the Impala, his eyes widening. The hunter runs towards the angel, wrapping his arms around his shoulders in a hug. Castiel put his arms around Dean’s waist, holding him tight and close. The hunter pulled away and looked in Castiel’s soft eyes. There was a faint blue glow in them, the glow of protection and care and power.

            “I’ve… I’ve been praying for you. Why didn’t you come? Crowley has Sam and who knows what kind of torture he’s going through.” Dean asked, glued to his angel. Castiel snapped his fingers and all three of them were in the Impala, Bobby in the back with Dean and Castiel in the front.

            “I had some angel business to deal with. You know there’s a war going on up there. It’s a mess and everyone depends on me. It’s such a mess up there.” The angel’s low voice carried through the car. Dean melted when he spoke.

            “What kind of mess is up there? Anything we should know about?” Bobby chimed in, giving the two weird looks.

            “Nothing you should worry yourself with right now. We need to focus on Sam.” Castiel said, almost lying through his teeth. He knew where Sam was. Sam was with Crowley in a room of pleasurable pain and sexual fantasies. Just thinking about this made Castiel steal a glance at Dean, wishing nothing more than to have that kind of privacy with him.

            “Where should we go first?” Dean asked, starting the Impala up and shifting into gear.

            “Back to the Men of Letters base.” He replied.

            Dean nodded, starting through the trees, the rumble of the engine filling the three’s ears with a familiar sound. Castiel felt his chest grow tight. He didn’t know how to process a care and worry about a human like this. He only ever cared for anyone like a brother or a father. But this was different. The way Dean’s eyes sparkled when he concentrated drove Castiel up the wall. He cared so much for this human, this human hunter. Not only did he want to protect, but he wanted to kiss, make love to, and provide for Dean. This was his human and he was going to do everything he possibly could to give him a comfortable life, given the circumstances. 


End file.
